


On The Road Again

by HyperKid



Series: Trans Caleb AU [3]
Category: Critical Role (Web Series)
Genre: Beau and Jester attempting to be subtle, Beau’s Binding Academy, Caleb Stop Hurting Himself Challenge 2019, Everything’s better with friends, Fluff, Other, Trans Caleb Widogast, Trans Male Character, cuz that goes well, it’s just easier to say we’re fucking
Language: English
Status: Completed
Published: 2019-06-11
Updated: 2019-06-11
Packaged: 2020-04-24 18:01:55
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,648
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19178539
Author URL: https://archiveofourown.org/users/HyperKid/pseuds/HyperKid
Summary: The Mighty Nein’s first night on the road, and everyone seems to want Caleb’s attention. The question is, how to explain it?





	On The Road Again

**Author's Note:**

> HK: I’m... being all productive? It’s kinda weird?   
> Mollymauk: I mean technically you’ve just got a lot of things reaching critical mass so they’re easy to finish.   
> HK: This is also true. I should be working on your tapestry though...   
> Mollymauk: Yeah but no one gets laid on the tapestry.   
> HK: ... I frankly do not believe you.   
> Mollymauk: So write me getting laid in the tapestry.   
> HK: THIS IS SABOTAGE *whips out a new note* 
> 
> WARNINGS!! Caleb is an angsty boy 
> 
> Disclaimer: I do not own anything and it’s a little bit sad

Secrets were a lot harder to keep out on the road. With no one else around, nothing but fields and forest as far as the eye could see, there was nothing for anyone to focus on but their companions. 

 

Caleb was grateful for Molly, both as a shiny and colourful distraction for all, and for being completely, openly disinterested in anyone else’s history. It seemed they all had something shady in their past to hide. 

 

On their first evening, Jester cheerfully offered to take the first watch, shooting Caleb a coy smile. It had been a quiet day, and he could guess what she wanted. 

 

Of course, Molly took a break from being helpful and volunteered to sit up with them, at least for a while. 

 

“It’s been a slow day, if either of you wants to sleep I’ll take the watch.” 

 

Jester hesitated, shooting an uncertain glance at Caleb. She wasn’t going to say anything, he realised, because she couldn’t be sure what would be more than he wanted said. A slow smile curled across Molly’s lips. 

 

“And of course, if both of you wanted to do something other than sleep... I promise not to peek.” 

 

It took a moment for Caleb to understand the implication, and when he did he flushed red to the tips of his ears. 

 

“No, no, I...” he paused, glancing across to Jester. It.... would be a convenient explanation that would not involve any of his own personal details. For a moment he imagined he saw a flash of hurt on her face, but it was covered near immediately by a sunny smile. 

 

“You’re so silly, Molly,” she laughed, patting the other tiefling on the arm. Both of his eyebrows rose, but before he could comment, Beau had wandered over. 

 

“Hey, Caleb, you got a minute?” Her gaze flicked from Jester to Molly, a brow of her own rising at the broadening grin on the lavender tiefling’s face. 

 

“You’re certainly popular,” Molly mused, leaning back on his elbows and decidedly enjoying Caleb’s flustered stuttering. An even broader grin spread across Jester’s face as she looked back from Beau, clapping her hands. 

 

“Oh yes! Caleb is verrrrrrry good with the ladies, aren’t you Caleb!” 

 

Caleb hunched his shoulders, doing his level best to hide in his scarf. 

 

“Another time, Beauregard,” he mumbled, eyes fixed on the ground in front of him. Molly waved a hand in their general direction, snickering a little. 

 

“No, no, by all means. If you’ve managed to set up a pair of dates the three of you should work it out.” 

 

Beau’s jaw dropped, but before she could speak, Jester leaned forwards, batting her lashes. 

 

“Bold of you to assume we didn’t get together to set up a date with him.” 

 

Molly’s brows rose to disappear under his hairline and he tossed his head back to cackle. 

 

“Fair, fair,” he admitted, wiping a tear from his eye. The two humans exchanged bemused glances, Caleb forgetting momentarily what she’d even come over for as the tieflings got going. 

 

Fjord meandered over, looking amused by the whole thing as well. 

 

“So should Molly and I take watch while the three of you...” he waggled his eyebrows suggestively, and Caleb groaned. 

 

“Fjord, it is not-“ he paused, startled, when Beau stepped on his foot. 

 

“Yeah, that’d be great,” the monk declared, folding her arms to glare defiantly up at the half orc. 

 

“No peeking,” Jester giggled, looping her arm through Caleb’s and tugging him to his feet. Caleb let himself be dragged away from camp into the bushes, shooting Nott a bemused shrug. Behind him, Molly stopped laughing long enough to give Fjord a nudge and a stage whisper. 

 

“I guess that’s what taking a bath will get ya.” 

 

The wizard’s cheeks flushed cherry red, but Jester gave his arm a quick squeeze and Beau linked though his other arm with such a fierce look on her face that he was briefly afraid. When he was sure they were out of earshot, he pulled the trio to a stop, frowning at Beau. 

 

“Are you sure you are alright with this? With them believing that we are...” his voice trailed off, unable to even find the words. Beau folded her arms and glowered at the ground. 

 

“Yeah, well, it shut them up an’ didn’t involve ratting you out, didn’t it?” She grumbled. It sent a warm jolt through Caleb’s chest; sure, they didn’t know each other very well. But she valued his secrets. 

 

Jester, completely unabashed by anything and everything, giggled and stretched her arms up and behind her head, rolling out her shoulders. 

 

“And it’s something we can claim to be doing every night.” A pair of gaping human expressions made her pause for a moment, cocking her head to one side. “What?” 

 

“Every night?” Caleb asked, somewhat weakly. 

 

“And in the afternoons, if you like,” Jester agreed brightly. Beau’s face had broken into a distinctly speculative grin as she looked her friend over, which was only returned. Caleb shook his head quickly, clasping his hands over his burning cheeks. 

 

“Look, we can talk about... frequency... at a later date. Beauregard, you wished to show me something?” 

 

The monk physically shook her head to break the connection, forcing her attention back to the wizard. 

 

“Right, yeah. I was gonna teach you how to bind better.” She shrugged out of her vest and paused, both hands on the bottom of her shirt. “You’re not gonna get weird if I get my boobs out, are you?” 

 

“I won’t!” Jester volunteered cheerfully, sticking a hand in the air. “Not while we’re helping Caleb, anyway.” 

 

“I don’t mind if you do,” Beau replied with a crooked smile. Caleb ran his hands over his face. 

 

“If you two would like to flirt I can always leave.” 

 

“We can flirt later,” Jester waved a hand dismissively, then paused. “Would you feel better if I left? I can come heal you later.” 

 

Beau’s eyes narrowed briefly at the mention of healing before her expression smoothed back out into indifference. The lack of judgement helped to settle Caleb a little and he began to relax to consider it. 

 

Both women already knew, and neither had been inclined to be anything but helpful. Part of him wanted to skip the whole thing and just keep going as he had been. Part of him knew that he was part of a group now, more than just his own life relying on him. The same reason he’d allowed Jester to stay on the first night. 

 

He gave Jester a slightly strained smile. 

 

“No, it... you may as well stay. We wouldn’t want Molly thinking you went unsatisfied.” There was a moment of surprised quiet, then Jester burst into giggles and Beau snorted most of a laugh through her nose. 

 

“Yeah, can’t have that,” the monk agreed, tossing off her shirt without a second thought. Caleb couldn’t help a moment’s jealousy. “I don’t think any of us’d survive his bullshit.” 

 

“I wouldn’t mind him showing me a good time,” Jester mused, dropping to sit on the ground, “but I’d like to watch this too, I haven’t actually seen anyone do it with the bandages. Mama has special binders because they’re safer,” she elaborated when Beau gave her a questioning look. 

 

Caleb took a seat beside her, mostly because he was unsure what else to do. Beau crossed her legs and sat across from them both, holding up the same bandage she’d used in Trostenwold. 

 

“Okay so, you paying attention?” The chilly autumn air on dark skin didn’t seem to be bothering her, but Caleb nodded quickly anyway. He wouldn’t want his own coat off long in this weather. Jester gave him a little nudge. 

 

“You should undo yours,” she murmured, giving Beau an apologetic smile. “And I can give you another healing spell. Just to be safe.” 

 

Caleb wavered for a moment, glancing back towards the camp. He would have to go back. Face Molly and Fjord. And Nott. Would have to take the time to rebind the next morning. 

 

Would be able to try out Beau’s new binding style the next morning. 

 

As though reading his mind, the monk nodded. 

 

“If we take last watch instead of first, I’ll help you wrap up in the morning. You can show me what you’ve learned.” There was a hint of mischief in her grin, and just a trace of rising awe. “Hey, I sound like a real teacher!” 

 

It broke any remaining tension, and Caleb snickered, shaking his head. 

 

“Almost like a professional,” he agreed. Beau huffed and punched his shoulder, then straightened up and raised her bandages again. 

 

“Shut up, we’ve just established there will be a test later.” 

 

“Can I try too?” Jester asked excitedly, bouncing a little in place. Caleb, half way between reaching under his shirt to loosen the knots, paused to look quizzically at Beau. Jester was... well. Bustier than either one of them. 

 

The monk herself didn’t seem to notice, busy giving Jester a considering look. 

 

“Well, not with the corset, but I don’t see why not. I can show Caleb on you tonight if you like?” 

 

This time it was Caleb’s turn to lose his brows under his bangs. 

 

“You think it will work?” 

 

Jester didn’t seem quite sure if this was an insult or not, but Beau just shrugged and nodded. 

 

“Not down to nothing, but yeah. It’s a practice kinda thing.” 

 

And it would put them all on equal footing. Caleb supposed that would help; it would be easier to bare his own skin knowing that both the ladies had already done the same, and wouldn’t bother judging. It was a nice thought. His skin could just be... well. Skin. Not something to be ashamed of or hide to protect himself. 

 

He managed a nod and Beau nodded back matter of factly. 

 

“Alright. Watch closely, alright? The idea is to spread out and down, flattening as much as possible before the bandages get into it. That means you gotta start a little weird.” 

 

Her instructions weren’t exactly what one would consider professional, being awkwardly worded and sometimes repeated a couple of times as she worked, trying to find the right phrasing. The first time Caleb stayed quiet, mostly listening and trying to watch. Trying to learn. 

 

He preferred reading to learn, personally, but it wasn’t his first practical lesson. 

 

Once Beau had tied off the wrap to her satisfaction she raised both her arms, twisting sideways to let them both take a look. 

 

“Alright, see? There’s basically nothing there, but I can still breathe and move. You gotta make sure you can get that finger in there at the end, or you’re risking a bunch of shit including cracked ribs.” 

 

Jester made a disgruntled noise, bouncing in place on the ground again. 

 

“I still think Mama’s are easier, but that’s really cool Beau! My turn!” When she’d begun loosening her armour was a big question, because she was suddenly tossing it off like it had never been attached, shoving the sleeves of her dress off her shoulders and down under her breasts. 

 

There wasn’t an ounce of hesitation anywhere in her, and it took both humans aback for a moment. Caleb averted his gaze, frowning over Jester’s head. Beau took a moment just to stare blankly before clearing her throat and waving the tiefling over. 

 

“Right, yeah, okay... and you’re good with me touching you?” She asked again, slightly hesitant and feeling a little strange to be hesitating. Jester nodded cheerfully and threw her hands above her head. 

 

“Where do you want my arms?” She asked brightly, not remotely self conscious. A slow grin spread across Beau’s face and she shook her head, shifting around behind her friend. Any kind of self consciousness melted away under Jester’s enthusiasm. 

 

“How about out to your sides, rather than straight up?” 

 

The tiefling complied immediately, raising her elbows and turning a beaming smile on Caleb. 

 

“It’s going to be so cool!” 

 

Caleb shook his head, a smile of his own tugging at his lips. He couldn’t imagine anything daunting her enthusiasm. 

 

He wasn’t sure where to look at first, as Beau began passing the bandage around Jester’s chest. The tiefling hummed happily, bouncing a little in place and staring down at herself, watching the cloth slowly cover her. 

 

“You know, I’m sure Beau could do yours for you if you asked nicely?” She pointed out, glancing up to grin at Caleb. Behind her, Beau shrugged, leaning around Jester to catch his eye. 

 

“If you wanted to?” The monk offered, a brow rising in question. Caleb hesitated for a moment, considering. Beau’s hands were quick, sure, and entirely business as she bound Jester’s chest, expertly wrapping around and over. Occasionally she paused, asking Jester to readjust herself a little, but after a couple of attempts it really didn’t seem necessary. 

 

It would be so nice not to care about showing skin again. 

 

Neither woman stopped to wait for him to answer, sitting quietly for what might have been the first time in Jester’s life to let him think while they worked. Beau was nearly finished by the time he nodded. 

 

“I think... that would be helpful, yes.” 

 

A rising worm of panic threatened to make an appearance, which Caleb hurriedly squashed. Now was not the time for a panic attack about Trent finding him; these were his friends. If he thought they would turn him in, they should not have been travelling together at all. 

 

Jester beamed and bounced a little at his words, earning her a light smack upside the head from her teammate. 

 

“Hey, watch it! Don’t undo all my hard work,” Beau chided her, then nodded to Caleb. 

 

“I can do you tonight if you like, and again tomorrow if you untie to go to bed?” 

 

Right. Because it was a bad idea to try and sleep with his chest bound. Caleb did his best to look like he’d been intending to untie all along. 

 

“That would be... very helpful, Beau, thank you.” It got him a slightly suspicious look, so it probably wasn’t fully convincing, but neither woman said anything. It was... nice, in a way. Not having to worry that something would slip, that he would have to run or hide. 

 

While he was ruminating, Beau had managed to finish her work, tying off the ends and nodding to Jester. 

 

“What do you think?” 

 

The tiefling ran her hands down her sides, twisting this way and that to admire the effect. 

 

“It’s a little difficult for me to see from this angle... can we do it at the next inn too, when we’ve got a mirror?” She pouted over her shoulder and Beau rolled her eyes, not bothering to hide her grin. 

 

“If you like. It’s not all that hard. And how does it feel?” 

 

This time Jester’s arms went straight up into the air, out and around in circles. 

 

“Kind of restricting,” she decided, leaning from side to side now too. Then she bounced to her feet, beaming down at Caleb. “What do you think, Caleb? Does it look good?” 

 

Completely unprepared for the question, Caleb felt his cheeks flush, gaping up at their cleric. And he had to admit... 

 

“It is very impressive, Beauregard,” he mumbled, torn between not gaping openly at Jester’s chest and wanting to examine in detail, getting a good look at the wrap. 

 

Because while not completely flat, Jester’s cleavage being decided more substantial than either of her human friends, the binding had molded soft curves into a more stocky, trim figure that slid down into her tummy in a smooth line. Caleb glanced down at his own chest despite himself, a moment of hope lighting him. 

 

If Beau could get that much done with so little effect on Jester... 

 

The tight bindings were a part of his punishment, part of him tried to remind himself, but to no avail. He knew they were doing more than just punishing him. It was hard to catch his breath, hard to move and run and fight alongside his companions. It wasn’t just his own life anymore. 

 

He could find plenty more ways to punish himself that wouldn’t put this tenuous alliance at risk. 

 

Something in the grin curling around the edges of Beau’s aloof expression suggested the monk was more pleased with the praise than she wanted to let on, and she nodded gruffly to Caleb. 

 

“You okay with stripping down too then, or should we look away?” 

 

Jester tossed herself to the ground beside him in a fit of giggles, reaching for her symbol. 

 

“Let me do your healing spell! We keep getting distracted.” Her fingertips began to glow as she reached out, her hand brushing Caleb’s shoulder companionably and sending a soothing rush of warmth through him. The wizard paused a moment, then shrugged out of his coat. 

 

“I don’t mind. I suppose you should see what you will be... working with.” It took an effort to keep his voice casual, and he may have lingered overlong on unwrapping his scarf. 

 

Jester took his coat, making a face as she held it at arms’ length. 

 

“Is that bat poop?” 

 

A slight smile tugged at the corners of Caleb’s mouth as he removed another layer, shrugging off his tunic. 

 

“It’s for a spell. We don’t all have an imaginary friend who can give us magic.” 

 

“You could if you wanted to,” she pointed out matter of factly, sitting cross legged with the coat laid carefully in front of her, “the Traveler loves meeting new people.” 

 

The two humans exchanged a speaking look, then Caleb pulled off the last layer between himself and the elements. The chill winter air raised goose bumps on his pale arms almost at once as he dropped the bandages and he shivered. 

 

“Could we keep this quick, Beauregard?” He asked, hovering uncertainly. Jester had moved immediately to sit in front of the monk, but he wasn’t sure about moving closer. 

 

She seemed to be having some very similar reservations, but took the offered bandages, making a face at the condition they were in, and shuffled closer. 

 

“You could make us another little fire?” She pointed out, nodding to Jester. “Jess can gather us some wood.” 

 

Caleb shook his head before the tiefling could begin to move. 

 

“Best not to. I do not want to draw attention to us. Besides... this will not take long?” 

 

Beau gave him a critical once over, then nodded and moved around behind him on her knees. 

 

“Yeah, I’ll wrap you real quick so you can have a look, then we’ll unwrap you so you can go get some sleep. Wouldn’t mind getting back to the fire myself.” 

 

Jester, entirely unaffected by the cold, grinned at both of them, her tail flicking through the air behind her. 

 

“We can always cuddle up to sleep if you guys are cold!” 

 

Caleb had to stifle a laugh as Beau’s hands froze, just visible on either side of his chest. He couldn’t tell if it was her own feelings or anticipation of his reaction that shocked her, but either way it was funny. As if they should have expected anything less from their cuddly cleric. 

 

His wrapping really didn’t take long, and with this third demonstration and more practical application he felt like he was beginning to understand the technique. It had a lot more to do with shaping his chest than his usual method of “wrap real tight and hope”, and the results were indeed impressive. He didn’t have a lot to hide in the first place, and while he couldn’t be sure without a mirror, he had to admit that from his perspective it looked at least as good. 

 

Jester gave it a very cheerful thumbs up of her own and proclaimed him “a slim and sexy beast”, which was worth it if only for Beau’s choked laughter. Any tension between them had relaxed over those few short minutes, and Caleb had to stifle a laugh of his own when the thought that they’d all been doing a different kind of bonding caught him off guard. 

 

Beau still made a point of checking that he untied the wrappings before redressing. Clearly she was also concerned about his more self destructive habits. But she didn’t comment on them or ask anything of him, which was the best the wizard felt he could hope for. 

 

Molly was on watch alone when they returned, making the expected salacious remarks. Jester immediately fell into cheerful and explicit details, punctuating them with a dramatic swoon that Beau only barely managed to catch. The monk seemed torn between embarrassed by the display and aggressively pushing detail on Molly, who lapped it all up. 

 

Caleb did his best impression of a rock, huddled up by the fire with Nott at his back, going over Beau’s stilted instructions in his mind. He would be doing it himself after their last watch, before any of the others woke. He’d need to get as much sleep as he could before then. 

 

**

 

Molly caught him the following morning when they were packing up the cart, a quick glance ensuring none of their companions were in earshot. 

 

“Look, I don’t care what you lot were actually doing and I’m not about to ask, I just wanted to check you didn’t mind me teasing Beauregard about being your dominatrix.” 

 

The bastard seemed completely unaffected by the words, and Caleb felt his lips twitching up into a smile in spite of himself. 

 

Maybe life with the group really could be this easy. 

 

“You can tease her about whatever you like, Mollymauk,” he told the tiefling earnestly, trying to fight a grin. Molly grinned back and patted him on the shoulder as he moved back to the campsite at large. 

 

“Don’t tell her I know you’re not fucking.” 

**Author's Note:**

> HK: Got another couple ideas in this vein in the works, gods only know when they’ll come out. I’m a busy bee!


End file.
